CN102718701A - 芳氧基二卤丙烯醚类化合物与应用 - Google Patents
芳氧基二卤丙烯醚类化合物与应用 Download PDFInfo
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- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Oc(cc1)ccc1O Chemical compound Oc(cc1)ccc1O QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- CVMPJJXTMRTPAV-UHFFFAOYSA-N CC(C)(C)N(C1=O)N=CC(Oc(cc2)ccc2O)=C1Cl Chemical compound CC(C)(C)N(C1=O)N=CC(Oc(cc2)ccc2O)=C1Cl CVMPJJXTMRTPAV-UHFFFAOYSA-N 0.000 description 1
- CPDLDKDKIUWVNA-BMPWDCPTSA-N CC(C)(C)N(C1=O)N=CC(Oc(cc2)ccc2OCCCOc(c(Cl)cc(OC/C=C(/Cl)\[ClH][ClH]/C(/Cl)=C\COc(cc2Cl)cc(Cl)c2OCCC[Br]=C)c2)c2Cl)=C1Cl Chemical compound CC(C)(C)N(C1=O)N=CC(Oc(cc2)ccc2OCCCOc(c(Cl)cc(OC/C=C(/Cl)\[ClH][ClH]/C(/Cl)=C\COc(cc2Cl)cc(Cl)c2OCCC[Br]=C)c2)c2Cl)=C1Cl CPDLDKDKIUWVNA-BMPWDCPTSA-N 0.000 description 1
- VRMUIVKEHJSADG-UHFFFAOYSA-N ClCc([s]1)cnc1Cl Chemical compound ClCc([s]1)cnc1Cl VRMUIVKEHJSADG-UHFFFAOYSA-N 0.000 description 1
- LVVQTPZQNHQLOM-UHFFFAOYSA-N Clc1nc(ccc(Cl)c2)c2[o]1 Chemical compound Clc1nc(ccc(Cl)c2)c2[o]1 LVVQTPZQNHQLOM-UHFFFAOYSA-N 0.000 description 1
- RKKKHBZUUXZHFB-UHFFFAOYSA-N Oc(cc1)ccc1OCc([s]1)cnc1Cl Chemical compound Oc(cc1)ccc1OCc([s]1)cnc1Cl RKKKHBZUUXZHFB-UHFFFAOYSA-N 0.000 description 1
- VMFCMPIPSNBHJH-UHFFFAOYSA-N Oc(cc1)ccc1Oc1nc(ccc(Cl)c2)c2[o]1 Chemical compound Oc(cc1)ccc1Oc1nc(ccc(Cl)c2)c2[o]1 VMFCMPIPSNBHJH-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明公开了一种芳氧基二卤丙烯醚类化合物,结构如通式(I)所示:
Description
技术领域
本发明属农用杀虫剂领域。具体地涉及一种芳氧基二卤丙烯醚类化合物与应用。
背景技术
众所周知,昆虫一般不仅在农业上造成农作物生长受损,也破坏建筑物和草坪,例如由土壤昆虫(例如白蚁和蛴螬)造成的损害。这种损害可导致相关的农作物、草坪或建筑物的数百万美元的损失。杀虫剂在防治昆虫中是有用的,但可能会对农作物例如小麦、玉米、大豆、马铃薯和棉花等造成显著的损害。从保护农作物角度出发,人类需要既能防治昆虫而且又不损害农作物,同时又对哺乳动物和其它活的生物无毒害作用的杀虫剂。
先正达公司的专利WO2005019147涉及如下通式所示的具有杀虫活性的化合物:
日本住友化学株式会社在专利WO9604228中公开了如下化合物A,其在500ppm的浓度下对斜纹夜蛾的致死率达80%以上,在100ppm浓度下对烟芽夜蛾的致死率高于80%;该专利同时公开了部分杀虫活性较高的化合物,在50ppm的浓度下对小菜蛾致死率达80%以上。其中通用名为pyridalyl的化合物已被开发为商品化杀虫剂。
化合物A
Pyridalyl
现有技术中,如本发明通式所示的化合物及其杀虫活性未见报道。
发明内容
本发明的目的在于提供一种结构新颖、杀虫活性更好的芳氧基二卤丙烯醚类化合物,它可用于制备杀虫剂以防治农业和其他领域中的害虫。
本发明的技术方案如下:
本发明提供一种芳氧基二卤丙烯醚类化合物,如通式(I)所示:
式中:
R1、R2、R3可相同或不同,分别选自H、卤素、C1-C8烷基或C3-C8环烷基;
X选自-CH2-、-CH2CH2-、-CH2CH2CH2-、-CH2CH2CH2CH2-、-CH2CH2CH2CH2CH2-、-CH(CH3)-、-CH(CH3)CH2-、-CH(CH3)CH2CH2-、-CH2CH2CH(CH3)-、-CH(C2H5)-、-C(CH3)2-、-CH(CH3)CH(CH3)-、-CH2C(CH3)2CH2-、-CH2CH2OCH2CH2-、-CH2CH2NHCH2CH2-、-CH2CH2SCH2CH2-、-CH2CH2SO2CH2CH2-、-CH2CH(OH)CH2-或-CH2COCH2-;
Q选自芳基或杂芳基,或者所述的芳基或杂芳基环上含有1-4个相同或不同的下述取代基:卤素、CN、NO2、羟基、C1-C8烷基、C3-C8环烷基、C1-C8卤代烷基、C1-C8烷氧基、C1-C8卤代烷氧基、C2-C8烯基、C2-C8炔基、C2-C8卤代烯基、C2-C8卤代炔基、C2-C8烯氧基、C2-C8炔氧基、C2-C8卤代烯氧基、C2-C8卤代炔氧基、芳基、COR5、CO2R4、CONR4R5、NR4R5、NR4COR5、NR5COR4、NR5CO2R4、NR5SO2R4、SOR5、SO2R5、SR5或SO2NR4R5;
R4选自H、C1-C8烷基、C1-C8卤代烷基或C3-C8环烷基;
R5选自H、C1-C8烷基、C1-C8卤代烷基,C3-C8环烷基、未取代或取代的芳基、未取代或取代的杂芳基,所述的取代基选自1-4个相同或不同的下述基团:卤素、CN、NO2、C1-C8烷基、C1-C8卤代烷基、C1-C8烷氧基、C1-C8卤代烷氧基、C1-C8烷氧基羰基或C1-C8烷基磺酰基;
n选自0、1或2。
本发明中较为优选的化合物为:通式(I)中
R1、R2、R3可相同或不同,分别选自H或卤素;
X选自-CH2-、-CH2CH2-、-CH2CH2CH2-、-CH2CH2CH2CH2-、-CH2CH2CH2CH2CH2-、-CH2CH(OH)CH2-或-CH2COCH2-;
Q选自芳基或杂芳基,或者所述的芳基或杂芳基环上含有1-4个相同或不同的下述取代基:卤素、CN、NO2、羟基、C1-C8烷基、C3-C8环烷基、C1-C8卤代烷基、C1-C8烷氧基、C1-C8卤代烷氧基、C2-C8烯基、C2-C8炔基、C2-C8卤代烯基、C2-C8卤代炔基、C2-C8烯氧基、C2-C8炔氧基、C2-C8卤代烯氧基、C2-C8卤代炔氧基、CO2R4、NR5SO2R4、SO2R5或SR5;
R4选自H、C1-C4烷基、C1-C4卤代烷基或C3-C6环烷基;
R5选自H、C1-C4烷基、C1-C4卤代烷基或C3-C6环烷基;
n选自0、1或2。
本发明进一步优选的化合物为:通式(I)中
R1、R2、R3可相同或不同,分别选自H、Cl或Br;
X选自-CH2-、-CH2CH2-、-CH2CH2CH2-、-CH2CH2CH2CH2-或-CH2CH2CH2CH2CH2-;
Q选自吡咯基、呋喃基、噻吩基、咪唑基、吡唑基、恶唑基、噻唑基、异恶唑基、异噻唑基、苯基、吡啶基、嘧啶基、哒嗪基、吡嗪基、哒嗪酮基、吲哚基、苯并呋喃基、苯并恶唑基、苯并噻吩基、苯并噻唑基、苯并异恶唑基、苯并异噻唑基、苯并咪唑基、苯并吡唑基或喹喔啉基,或者被1-3个独立选自以下基团进一步取代的上述基团:卤素、CN、NO2、羟基、C1-C8烷基、C3-C8环烷基、C1-C8卤代烷基、C1-C8烷氧基、C1-C8卤代烷氧基、C1-C4烷基硫基、C2-C6烯基、C2-C6炔基、C2-C6卤代烯基、C2-C6卤代炔基、C2-C6烯氧基、C2-C6炔氧基、C2-C6卤代烯氧基或C2-C6卤代炔氧基;
n选自0或1。
本发明更进一步优选的化合物为:通式(I)中
R1、R2、R3可相同或不同,分别选自H或Cl;
X选自-CH2-、-CH2CH2-、-CH2CH2CH2-或-CH2CH2CH2CH2-;
Q选自咪唑基、吡唑基、恶唑基、噻唑基、异恶唑基、异噻唑基、苯基、吡啶基、嘧啶基、哒嗪基、哒嗪酮基、吲哚基、苯并呋喃基、苯并恶唑基、苯并噻唑基、苯并异恶唑基、苯并异噻唑基、苯并咪唑基、苯并吡唑基或喹喔啉基,或者被1-3个独立选自以下基团进一步取代的上述基团:卤素、CN、NO2、羟基、C1-C4烷基、C3-C6环烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷基硫基、C2-C4烯基、C2-C4炔基、C2-C4卤代烯基、C2-C4卤代炔基、C2-C4烯氧基、C2-C4炔氧基、C2-C4卤代烯氧基或C2-C4卤代炔氧基;
n选自0或1。
本发明再进一步优选的化合物为:通式(I)中
R1、R2、R3可相同或不同,分别选自H或Cl;
X选自-CH2-、-CH2CH2-、-CH2CH2CH2-或-CH2CH2CH2CH2-;
Q选自噻唑基、苯基、吡啶基、嘧啶基、哒嗪基、哒嗪酮基、苯并恶唑基、苯并异噻唑基或喹喔啉基,或者被1-3个独立选自以下基团进一步取代的上述基团:F、Cl、Br、I、CN、NO2、羟基、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷基硫基、C2-C4烯基、C2-C4炔基、C2-C4卤代烯基、C2-C4卤代炔基、C2-C4烯氧基或C2-C4炔氧基;
n选自0或1。
更进一步地,本发明的优选化合物为:通式(I)中
R1、R2、R3可相同或不同,分别选自H或Cl;
X选自-CH2CH2CH2-;
Q选自噻唑基、苯基、吡啶基、嘧啶基、哒嗪基、哒嗪酮基、苯并恶唑基、苯并异噻唑基或喹喔啉基,或者被1-3个独立选自以下基团进一步取代的上述基团:F、Cl、Br、CN、NO2、CH3、C2H5、C(CH3)3、CF3、CHFCH3、CHF2、OCH3、OCF3、OCHF2或SCH3;
n选自0或1。
本发明最优选的化合物为:通式(I)中
R1、R2、R3可相同或不同,分别选自H或Cl;
X选自-CH2CH2CH2-;
Q选自噻唑基、苯基、吡啶基、哒嗪酮基或苯并恶唑基,或者被1-3个独立选自以下基团进一步取代的上述基团:F、Cl、Br、CH3、C2H5、C(CH3)3、CF3、CHFCH3或CHF2;
n选自0或1。
上面给出的通式(I)化合物的定义中,汇集所用术语一般定义如下:
卤素:指氟、氯、溴或碘。烷基:直链或支链烷基,例如甲基、乙基、正丙基、异丙基或不同的丁基、戊基或己基异构体。环烷基:具有3至8个碳原子的单环饱和烃基,例如环丙基、环丁基、环戊基或环己基等。卤代烷基:直链或支链烷基,在这些烷基上的氢原子可部分或全部被卤原子所取代,例如氯甲基、二氯甲基、三氯甲基、氟甲基、二氟甲基、三氟甲基或七氟异丙基。烷氧基:直链或支链烷基,经氧原子键连接到结构上,例如甲氧基、乙氧基、叔丁氧基等。卤代烷氧基:直链或支链烷氧基,在这些烷氧基上的氢原子可部分或全部被卤原子所取代,例如氯甲氧基、二氯甲氧基、三氯甲氧基、氟甲氧基、二氟甲氧基、三氟甲氧基、氯氟甲氧基、三氟乙氧基等。烯基:包括直链或直链烯类,如乙烯基、1-丙烯基、2-丙烯基和不同的丁烯基、戊烯基和己烯基异构体;烯基还包括多烯类如1,2-丙二烯基和2,4-己二烯基。炔基:包括直链或支链炔类,如乙炔基、1-丙炔基和不同的丁炔基、戊炔基和己炔基异构体;炔基还包括由多个三键组成的基团,例如2,5-己二炔基。卤代烯基:可被卤原子取代至少一个多个氢原子的烯基。卤代炔基:可被卤原子取代至少一个或多个氢原子的炔基。烷氧基羰基:烷基-O-CO。烯氧基:直链或支链烯基,经氧原子键连接到结构上,例如丙烯氧基。炔氧基:直链或支链炔基,经氧原子键连接到结构上,例如丙炔氧基。卤代烯氧基:直链或支链烯氧基,在这些烯氧基上的氢原子可部分或全部被卤原子所取代。卤代炔氧基:直链或支链炔氧基,在这些炔氧基上的氢原子可部分或全部被卤原子所取代。烷基氨基:是例如甲基氨基、乙基氨基、正丙基氨基、异丙基氨基或同分异构的丁基胺。烷基磺酰基:烷基-S(O)2-。
芳基:包括苯基或萘基等。
杂芳基:指含1个或多个N、O、S杂原子的五元环或六元环。例如吡咯基、呋喃基、噻吩基、咪唑基、吡唑基、恶唑基、噻唑基、异恶唑基、异噻唑基、吡啶基、嘧啶基、哒嗪基、哒嗪酮基、吲哚基、苯并呋喃基、苯并恶唑基、苯并噻吩基、苯并噻唑基、苯并异恶唑基、苯并异噻唑基、苯并咪唑基、苯并吡唑基、喹喔啉基等。
本发明通式(I)化合物中部分优选的Q基团上具体取代基例举见表1-表15:
式中其他各基团定义同前。
当Q选自吡啶基时,环上的取代基见表1-表3;当Q选自苯基时,环上的取代基见表4;当Q选自嘧啶基时,环上的取代基见表5-表6;当Q选自吡嗪或喹喔啉基时,环上的取代基见表7;当Q选自哒嗪基时,环上的取代基见表8;当Q选自吡唑基时,环上的取代基见表9-表10;当Q选自噻唑、恶唑、咪唑、苯并噻唑、苯并咪唑或苯并恶唑基时,环上的取代基见表11-表12;当Q选自噻吩、吡咯、呋喃、苯并噻吩、吲哚或苯并呋喃基时,环上的取代基见表13-表14;当Q选自哒嗪酮基时,环上的取代基见表15。
表1
R | R | R | R | R |
3-CH3 | 4-Br | 6-OCH3 | 3-CH3-5-NO2 | 6-CH3-3,5-2Br |
4-CH3 | 5-Br | 5-OCH3 | 4-CH3-3-NO2 | 3-CONH2-4,6-2Cl |
5-CH3 | 6-Br | 3,5-2Cl | 4-CH3-5-NO2 | 4-CH3-5-NO2-3-Br |
6-CH3 | 5-I | 3,5-2Br | 5-CH3-3-NO2 | 3-CN-4,6-2Cl |
3-Cl | 5-F | 4-CH3-5-Br | 6-CH3-4-NO2 | 3-CN-4-CH3-6-Cl |
4-Cl | 6-F | 6-CH3-5-CN | 6-CH3-5-NO2 | 3-CN-4-CF3-6-Cl |
5-Cl | 3-CN | 3,5,6-3Cl | 3-NO2-5-Cl | 4-CH3-5-CN-6-Cl |
6-Cl | 4-CN | 3-CO2CH3 | 3-NO2-5-Br | 4-CF3-5-CN-6-Cl |
3-CF3 | 5-CN | 5-CO2CH3 | 5-NO2-3-Br | 3-CO2CH3-6-Cl |
4-CF3 | 6-CN | 3,5-2Cl-6-OCH3 | 5-CH3-3-Br | 5-CO2CH3-6-Cl |
5-CF3 | 3-NO2 | 5-CF3-3-Cl | 6-CH3-5-Br | 5-CF3-3,6-2Cl |
6-CF3 | 5-NO2 | 5-CN-3-Cl | 3-CH3-5-Br | 5-CF3-6-Cl |
3-Br | 6-NO2 | 5-CH3-3-Cl | 3-CF3-6-Cl | 3-CN-6-Cl |
表2
R | R | R | R | R |
5-Cl | 6-CF3 | 6-CH3 | 6-OCH3 | 6-SO2CH3-5-Cl |
2-Cl | 4-CF3 | 2,4-2Cl | 6-CH3-2-Cl | 6-NHCH3-5-Cl |
6-Cl | 4-CH3 | 6-CN | 2-OCH2CF3 | 6-OCH3-2-Cl |
2-Br | 2-OCH3 | 2-OCHF2 | 6-OCHF2 | 4-CF3-2,6-2Cl |
6-Br | 2,5-2Cl | 2-CF3 | 6-OCH2CF3 | 4-CH3-2,6-2Cl |
2-CH3 | 2,6-2Cl | 5-CH3-2-Cl | 5-Cl-2-CN | 6-CH3-2,4-2Cl |
2-CN | 5,6-2Cl | 4-CH3-2-Cl | 6-CF3-2-Cl | 6-CF3-2,4-2Cl |
表3
R | R | R | R |
2-F | 2-CH3 | 2-Cl-3-CN-6-CH3 | 5,6-(CH=CH-CH=CH-) |
2-Cl | 2-OCH3 | 2,6-2OCH3 | 2,3-2CH3-5,6-(CH=CH-CH=CH-) |
2-Br | 2-OCHF2 | 2-OC(CH3)3 | 2-CH3-5,6-(CH=CH-CH=CH-) |
2-I | 2-OCF3 | 2-OCH2CF3 | 2-CF3-5,6-(CH=CH-CH=CH-) |
3-Cl | 2,6-2Cl | 2-Cl-5-NO2 | 2,3-2CH3-5,6-(CH=CF-CH=CF-) |
3-Br | 3,5-2Cl | 2-Cl-3,5-2NO2 | 2,3-2CH3-5,6-(CH=CF-CH=CH-) |
3-NO2 | 2-Cl-3-CN | 2,6-2F | 2-CF3-5,6-(CH=CF-CH=CH-) |
2-CN | 3,5-2OCH3 | 2-OCH3-6-Cl | 2-CH3-5,6-(CH=CF-CH=CH-) |
3-CN | 3-CN-2-OCH3 | 2-NHCH3-6-Cl | 5,6-(CH=CF-CH=CF-) |
2-CF3 | 2-Cl-3-NO2 | 3-Cl-6-NO2 | 5,6-(CH=Cl-CH=CH-) |
表4
R | R | R | R | R | R | R |
4-CN | 4-NO2 | 2-SO2C2H5 | 2,3-2F | 2,3-2CH3 | 2-Cl-4-F | 4-CH3-2-Br |
2-F | 2-CN | 3-SO2C2H5 | 2,4-2F | 2,4-2CH3 | 2-Cl-4-Br | 4-CH3-2-Cl |
3-F | 3-SCF3 | 4-SO2C2H5 | 2,5-2F | 2,5-2CH3 | 2-Cl-4-I | 2,4,6-3CH3 |
4-F | 4-SCF3 | 2-CO2CH3 | 2,6-2F | 2,6-2CH3 | 3-Cl-4-I | 2,4,6-3C2H5 |
2-Cl | 2-OC2H5 | 3-CO2CH3 | 3,4-2F | 3,4-2CH3 | 4-Cl-2-Br | 2-NHCOCH3 |
3-Cl | 3-OC2H5 | 4-CO2CH3 | 3,5-2F | 3,5-2CH3 | 3,4,5-3F | 3-NHCOCH3 |
4-Cl | 4-OC2H5 | 2-CO2C2H5 | 2,3-2Cl | 2,3-2C2H5 | 2,3,4-3Cl | 4-NHCOCH3 |
2-Br | 2-O(CH3)3 | 3-CO2C2H5 | 2,4-2Cl | 2,4-2C2H5 | 2,3,5-3Cl | 2-NHSO2CH3 |
3-Br | 3-O(CH3)3 | 4-CO2C2H5 | 2,5-2Cl | 2,5-2C2H5 | 2,3,6-3Cl | 3-NHSO2CH3 |
4-Br | 4-O(CH3)3 | 2-N(CH3)2 | 2,6-2Cl | 2,6-2C2H5 | 2,4,5-3Cl | 4-NHSO2CH3 |
2-I | 2-OCHF2 | 3-N(CH3)2 | 3,4-2Cl | 3,4-2C2H5 | 2,4,6-3Cl | 2-CH(CH3)2 |
3-I | 2-C(CH3)3 | 4-N(CH3)2 | 3,5-2Cl | 3,5-2C2H5 | 3,4,5-3Cl | 3-CH(CH3)2 |
4-I | 3-C(CH3)3 | 2-N(C2H5)2 | 2,3-2Br | 3,4-2CF3 | 2,3,4-3Br | 4-CH(CH3)2 |
2-CH3 | 4-C(CH3)3 | 3-N(C2H5)2 | 2,4-2Br | 3,5-2CF3 | 2,3,5-3Br | 2-CF3-4-Cl |
3-CH3 | 2-COCH3 | 4-N(C2H5)2 | 2,5-2Br | 2,6-2SCF3 | 2,3,6-3Br | 2-CF3-4-Br |
4-CH3 | 3-COCH3 | 2,3-2OCH3 | 2,6-2Br | 3,4-2SCF3 | 2,4,5-3Br | 3-CF3-4-NO2 |
2-C2H5 | 4-COCH3 | 2,4-2OCH3 | 3,4-2Br | 3,5-2SCF3 | 2,4,6-3Br | 3-CF3-4-F |
3-C2H5 | 2-COC2H5 | 2,5-2OCH3 | 3,5-2Br | 2,3-2SCH3 | 4-CH3-3-F | 3-CF3-4-Cl |
4-C2H5 | 3-COC2H5 | 2,6-2OCH3 | 2,3-2CN | 2,4-2SCH3 | 4-CH3-3-Cl | 4-CF3-2-NO2 |
2-CF3 | 4-COC2H5 | 3,4-2OCH3 | 2,4-2CN | 2,5-2SCH3 | 4-CH3-3-Br | 4-CF3-2-Cl |
3-CF3 | 2-SOCH3 | 3,5-2OCH3 | 2,5-2CN | 2,6-2SCH3 | 2-CH3-3-F | 4-CF3-2-Br |
4-CF3 | 3-SOCH3 | 3-CONH2 | 2,6-2CN | 3,4-2SCH3 | 2-CH3-3-Cl | 2-CH3-5-NO2 |
2-OCH3 | 4-SOCH3 | 4-CONH2 | 3,4-2CN | 3,5-2SCH3 | 2-CH3-4-F | 2-CH3-3-NO2 |
3-OCH3 | 2-SO2CH3 | 2,4-2NO2 | 3,5-2CN | 2,3-2OCF3 | 2-CH3-4-Cl | 2-SCH3-5-Cl |
4-OCH3 | 3-SO2CH3 | 2,5-2NO2 | 2-F-4-Cl | 2,4-2OCF3 | 2-CH3-4-Br | 4-SO2CH3-2Cl |
2-SCH3 | 4-SO2CH3 | 2,6-2NO2 | 2-F-4-Br | 2,5-2OCF3 | 2-CH3-5-F | 2-CH3-4-NO2 |
3-SCH3 | 2-SOC2H5 | 3,4-2NO2 | 2-F-4-I | 2,6-2OCF3 | 2-CH3-5-Cl | 2-CH3-4-OCH3 |
4-SCH3 | 3-SOC2H5 | 3,5-2NO2 | 2-F-5-Cl | 3,4-2OCF3 | 2-CH3-5-Br | 2-CH3-6-C2H5 |
2-OCF3 | 4-SOC2H5 | 2,3,6-3F | 3-F-5-Cl | 3,5-2OCF3 | 2-CH3-6-Cl | 2-CH3-6-NO2 |
3-OCF3 | 3-OCHF2 | 2,4,5-3F | 4-F-3-Cl | 2,3-2SCF3 | 3-CH3-2-Br | 2,4,6-3NO2 |
4-OCF3 | 4-OCHF2 | 2,4,6-3F | 2,3-2CF3 | 2,4-2SCF3 | 3-CH3-4-Cl | 2,3-2Cl-4-Br |
2-CN | 2,3-2NO2 | 2,3,4-3F | 2,4-2CF3 | 2,5-2SCF3 | 3-CH3-4-Br | 2,4-2F-6-Cl |
3-CN | 2-NO2 | 2,3,5-3F | 2,5-2CF3 | 2,4,6-3CF3 | 3-CH3-4-I | 2-NO2-4,6-2Br |
4-CN | 3-NO2 | 4-F-6-Cl | 2,6-2CF3 | 3,4,5-3Br | 2-CH3-4-I | 2-NO2-4-F |
续表4
R | R | R | R |
2-CN-3-F | 4-CH3-2-NO2 | 2,4-2NO2-6-Cl | 3-CH3-4-NHCOCH3 |
2-CN-3-Cl | 4-CH3-3-NO2 | 2,4-2NO2-6-Br | 4-CH3-3-NHSO2CH3 |
2-CN-4-Cl | 5-CH3-2-CN | 3,4-2CH(CH3)2 | 5-CH3-2-OCH3-4-Cl |
2-CN-4-Br | 2-CF3-4,6-2Cl | 3,5-2CH(CH3)2 | 5-CF3-2-NHCOCH3 |
5-CH3-2-F | 2-CF3-4,6-2Br | 2-NO2-4-OCH3 | 2-CH3-4-NO2-6-Cl |
4-CN-2-Cl | 3-CH3-2,6-2Cl | 2-NO2-4-OC2H5 | 2-CH3-4-NO2-6-Br |
2-F-3-Cl | 2-CH3-4,6-2Br | 4-CH3-2,6-2Br | 2-CH3-6-NO2-4-Cl |
2,3,5,6-4F | 2-CH2C≡CH | 5-CH3-4-F-6-Cl | 2-CH3-6-NO2-4-Br |
5-CF3-2-Cl | 3-CH2C≡CH | 4-C(CH3)3-2-Cl | 2,5-2OCH3-4-NO2 |
5-CF3-2-Br | 4-CH2C≡CH | 4-CF3-2-Cl-6-Br | 2,6-2CH3-4-C(CH3)3 |
2-CN-4-NO2 | 2-OCH3-5-Cl | 2-CO2CH3-4-Br | 4-CF3-2-NO2-5-Cl |
4-CN-2-CF3 | 4-OCH3-3-F | 4-CO2CH3-2-Cl | 4-CF3-2-NO2-6-Cl |
4-CN-2-NO2 | 4-OCH3-3-Cl | 4-CO2CH3-2-Br | 4-CF3-2-NO2-6-Br |
5-NO2-2-F | 2-OCF3-4-CN | 2,4,6-3CH(CH3)2 | 5-NHCOCH3-2-Cl |
2-NO2-6-Cl | 2-OCF3-4-Cl | 2,4,6-3C(CH3)3 | 4-O(CH2)2N(CH3)2 |
2-NO2-4-Cl | 2-OCF3-4-Br | 2,3-2CH3-6-NO2 | 2-CH2C(CH3)=CH2 |
2-NO2-4-Br | 2-F-4,6-2Br | 2,4-2OCH3-5-Cl | 3-CH2C(CH3)=CH2 |
2-NO2-5-Cl | 4-OCF3-2-Cl | 2-OCH2C≡CI | 4-CH2C(CH3)=CH2 |
3-NO2-4-Cl | 4-OCF3-2-Br | 4-N(CH3)2-2-NO2 | 4-O(CH2)3CH3-2-NO2 |
3-NO2-4-Br | 4-F-2,6-2Br | 5-N(CH3)2-2-NO2 | 3-OCH3-4-CO2CH3 |
4-NO2-2-Cl | 2,4-2F-6-Cl | 4,5-2CH3-2-NO2 | 2-CH(CH3)CH2CH(CH3)2 |
5-NO2-2-Cl | 4-NO2-2-OCH3 | 2-NO2-4-F-5-Cl | 2,3-(CH2CH2CH2-) |
5-NO2-2-Br | 2-CH2CH=CH2 | 2-CN-4-NO2-6-Cl | 2,3-(CH2CH2CH2CH2-) |
3-NO2-4-F | 3-CH2CH=CH2 | 2-CN-4-NO2-6-Br | 2,3-(CH=CH-CH=CH-) |
4-SO2NH2 | 4-CH2CH=CH2 | 2-OCH2CH=CH2 | 4,5-(CH=CH-CH=CH-) |
2,4,6-3OCH3 | 2-C(CH3)=CH2 | 3-OCH2CH=CH2 | 2,3-(CCl=CH-CH=CH-) |
3,4,5-3OCH3 | 3-C(CH3)=CH2 | 4-OCH2CH=CH2 | 4,5-(CCl=CH-CH=CH-) |
2,4,6-3SCH3 | 4-C(CH3)=CH2 | 2-OCH2C≡CH | 2,3-(CH=CCl-CH=CH-) |
2,4,6-3OCF3 | 2-F-4-Cl-6-Br | 3-OCH2C≡CH | 4,5-(CH=CCl-CH=CH-) |
2,4,6-3SCF3 | 2,3,5,6-4F-4-CF3 | 4-OCH2C≡CH | 2,3-(CH=CH-CCl=CH-) |
3-CH3-2-Cl | 5-CF3-2-OCH3 | 5-NO2-2-OCH3 | 4,5-(CH=CH-CCl=CH-) |
2,3-2C(CH3)3 | 4-CN-2,6-2Cl | 5-CH3-2-OCH3 | 2,3-(CH=NO2-CH=CH-) |
2,4-2C(CH3)3 | 4-CF3-2,6-2Cl | 4-COCH3-2,6-2Cl | 4,5-(CH=NO2-CH=CH-) |
2,5-2C(CH3)3 | 4-CF3-2,6-2Br | 4-OCF3-2-NO2 | 2,3-(CH=CN-CH=CH-) |
2,6-2C(CH3)3 | 2,3,4,5,6-5Cl | 6-NO2-2,3,4-3F | 4,5-(CH=CN-CH=CH-) |
3,4-2C(CH3)3 | 5-CH3-2-CONH2 | 4-NO2-2,6-2Br | 2,3-(CH=CH3-CH=CH-) |
3,5-2C(CH3)3 | 2-CH3-5-CONH2 | 4-NO2-2,5-2Cl | 6-Cl-2,3-(CH=CH-CH=CH-) |
4-O(CH2)3CH3 | 2,3-2CH(CH3)2 | 4-F-3-Cl-2,6-2Br | 6-Cl-2,3-(CCl=CH-CH=CH-) |
2-CN-4,6-2Cl | 2,4-2CH(CH3)2 | 2,3-(OCF2O-) | 6-NO2-2,3-(CH=CH-CH=CH-) |
2-CN-4,6-2Br | 2,5-2CH(CH3)2 | 2,3-(OCH2O-) | 6-NO2-4,5-(CH=CH-CH=CH-) |
2-CF3-4-NO2 | 2,6-2CH(CH3)2 | 3,4-(OCH2O-) | 6-CN-2,3-(CH=CH-CH=CH-) |
5-CONH2-2-Cl | 4-NO2-2,6-2Cl | 3,4-(OCF2O-) | 6-CN-4,5-(CH=CH-CH=CH-) |
表5
R | R | R | R | R |
2-CH3 | 2-CN-6-Cl | 2-CH3-6-C2H5 | 2-CH(CH3)2-6-Cl | 2-(cyclopropyl)NH-6-CF3 |
2-Cl | 2-CH3-6-Cl | 2-NH2-6-OCH3 | 2-CN-5,6-2CH3 | 2-(cyclopropyl)-6-Cl |
2-CN | 2-CH3-6-OH | 2-CN-6-CH3 | 2-SO2CH3-6-CF3 | 2-(cyclopropyl)-6-CH3 |
2-NH2 | 2-CH3-6-CN | 2-SCH3-5-Br | 2-SO2CH3-6-CH3 | 2-(cyclopropyl)-5-Cl-6-CH3 |
2-C2H5 | 2-CN-6-CF3 | 5-NH2-6-Cl | 2-CF3-5,6-2CH3 | 2-(cyclopropyl)-5-Cl-6-C2H5 |
6-Cl | 5-Cl-2-NH2 | 2-SCH3-5-Cl | 2-CF3-5-CO2C2H5 | 2-(cyclopropyl)-5,6-2Cl |
6-OH | 2-NH2-6-CH3 | 2-SCH3-6-Cl | 2-CN-5-CH3-6-Cl | 2-CH3-5-Cl-6-CF3 |
5-CH3 | 2-NH2-6-CF3 | 2-SCH3-6-CF3 | 2-CONH2-6-CH3 | 2-CH3-5-Cl-6-CH3 |
5-Cl | 2,6-2NH2 | 2-SCH3-6-NH2 | 2-CONH2-6-CF3 | 2-CH3-5-Cl-6-C2H5 |
6-C2H5 | 2-NH2-6-Cl | 2-SCH3-6-CH3 | 2-SCH3-5-OH-6-Cl | 2-CH3-5-Cl-6-CHFCH3 |
5,6-2Cl | 5-Cl-6-CH3 | 5-Cl-6-C2H5 | 5-Cl-6-CF3 | 2-CH3-5-Cl-6-CHF2 |
6-CHF2 | 6-CHFCH3 | 5,6-2Cl-2NH2 | 5-Cl-6-CHFCH3 | 2-CH3-5-Cl-6-OCHF2 |
6-CF3 | 6-OCHF2 | 5-Cl-6-OCHF2 | 6-cyclopropyl | 2-CH3-5-Cl-6-OCH3 |
6-CN | 6-OCH3 | 6-OC(CH3)3 | 5-Cl-6-OCH3 | 5-Cl-6-CN |
表6
R | R | R | R | R |
4-Cl | 4,6-2CH3 | 4-CO2CH3 | 4-NH2-5-CN | 4-CH3-6-CO2C2H5 |
4-CH3 | 4,6-2Cl | 4,6-2OCH3 | 4-CHF2-6-Cl | 4-CF3-5-CO2CH3 |
4-CF3 | 4-Cl-5-Br | 5-CO2CH3 | 4-CH3-5,6-2Cl | 4,5-(CH=CH-CH=CH-) |
4-C2H5 | 4,5,6-3Cl | 4-Cl-6-CH3 | 4-C2H5-5,6-2Cl | 4,5-(CH=CH-CH=CH-) |
5-Cl | 4-CH3-6-Cl | 5-CN | 4-CHF2-5,6-Cl | 4,5-(CH=CH-CH=CH-)-6-Cl |
5-Br | 4-CF3-6-Cl | 4-CN | 4-CH3-6-CN | 4,5-(CH=CH-CCl=CH-)-6-Cl |
4-CHF2 | 4,5,6-3Cl | 4-OCH3 | 4-OCH3-6Cl | 4,5-(C(CH3)=CH-CH=CH-)-6-Cl |
表7
R | R | R | R |
5-Br | 5-CH3 | 3-CH3 | 5,6-(CH=CCl-CH=CH-) |
5-Cl | 5-NH2 | 3-CN | 5,6-(CH=CH-CH=CH-) |
5-CN | 5-SCH3 | 3-CF3 | 3-Cl-5,6-(CH=CH-CH=CH-) |
6-Cl | 6-SCH3 | 3,5-2Cl | 5,6-(CCF3=CH-CH=CH-) |
6-CN | 5-OCH3 | 3-Cl-5-CH3 | 5,6-(CCH3=CH-CH=CH-) |
3-Cl | 6-OCH3 | 3,5-2OCH3 | 5,6-(CCN=CH-CH=CH-) |
3-Br | 5,6-2CH3 | 5-Cl-3-CN | 5,6-(CI=CH-CH=CH-) |
表8
R | R | R | R | R |
6-CN | 6-CF3 | 4-CH3-6-Cl | 6-OCH2CF3 | 4,5-(CH=CH-CH=CH-) |
6-Cl | 6-SCH3 | 6-CH3-4-Cl | 6-OC(CH3)3 | 4,5-(CH=CH-CH=CH-)-6-Cl |
6-CH3 | 6-OCH3 | 6-NHCH3 | 4-CN-6-Cl | 4,5-(CH=CH-CH=CH-)-6-OCH3 |
6-NH2 | 4-NO2 | 6-CHF2 | 4-NO2-6-Cl | 4,5-(CH=CCl-CH=CH-)-6-Cl |
6-Br | 5-NO2 | 6-OCHF2 | 5-NO2-6-Cl | 5,6-(CH=CH-CH=CH-) |
表9
R | R | R | R | R |
3-CHF2 | 4-NO2 | 3-C2H5-4-Cl | 3-CH3-4-CN | 3,4-(CH2CH2CH2CH2-) |
3-CH3 | 4-CN | 3-CH3-4-Cl | 3-CH3-4-CN | 3,4-(CH=CH-CH=CH-) |
3-CF3 | 3-C(CH3)3 | 3-CH3-4-Br | 3-CF3-4-CH3 | 3,4-(CH=CCl-CH=CH-) |
3-C2H5 | 3,4-2CH3 | 3-CH3-4-NO2 | 3-CF3-4-Cl | 3,4-(CH=CH-CCl=CH-) |
表10
R | R | R | R | R |
3-CHF2 | 3-CH3-5-Cl | 3,5-2CH3 | 5-CHF2 | 3-CF3 |
3-CF3-5-Cl | 3-NH2 | 3-CH3 | 5-Cl | 3-CF3-5-OCHF2 |
表11
R | R | R | R |
4-Br | 4-CF3-5-CN | 4,5-(CCl=CH-CH=CH-) | 4,5-(CH=CH-CCF3=CH-) |
5-Cl | 4-CH2CO2C2H5 | 4,5-(CH=CCl-CH=CH-) | 4,5-(CH=CH-CNO2=CH-) |
5-CH3 | 4-CH3-5-COCH3 | 4,5-(CH=CH-CCl=CH-) | 4,5-(CMe=CH-CCl=CH-) |
4-Cl | 4-CH3-5-CO2C2H5 | 4,5-(CMe=CH-CH=CH-) | 4,5-(CH=CMe-CCN=CH-) |
5-Br | 4-CF3-5-CO2C2H5 | 4,5-(CH=CMe-CH=CH-) | 4,5-(CMe=CH-CNO2=CH-) |
4-CH3 | 5-CH3-4-CO2C2H5 | 4,5-(C(OMe)=CH-CH=CH-) | 4,5-(CCl=CMe-CH=CH-) |
5-NO2 | 4-CH3-5-CONHCH3 | 4,5-(CH=C(OMe)-CH=CH-) | 4,5-(CMe=CH-CNO2=CH-) |
5-OCH3 | 4-CF3-5-CONHCH3 | 4,5-(CCF3=CH-CH=CH-) | 4,5-(CCN=CMe-CH=CH-) |
4,5-2Cl | 4,5-(CH=CH-CH=CH-) | 4,5-(CNO2=CH-CH=CH-) | 4,5-(CCF3=CH-CCl=CH-) |
4,5-2CH3 | 4,5-(CCN=CH-CH=CH-) | 4,5-(CBr=CH-CH=CH-) | 4,5-(CCN=CCF3-CH=CH-) |
4-C(CH3)3 | 4,5-(CH=CBr-CH=CH-) | 4,5-(CH=CCN-CH=CH-) | 4,5-(CCF3=CH-CCN=CH-) |
4,5-(CH2-)3 | 4,5-(CCl=CH-CCl=CH-) | 4,5-(CH=CCF3-CH=CH-) | 4,5-(CCl=CCF3-CH=CH-) |
4,5-(CH2-)4 | 4,5-(CH=CH-CBr=CH-) | 4,5-(CH=CNO2-CH=CH-) | 4,5-(CCN=CCl-CH=CH-) |
4-CO2C2H5 | 4,5-(CH=CH-CCN=CH-) |
表12
R | R | R | R | R |
2-CN | 2-NO2 | 4-CO2C2H5 | 2-CF3-4-CO2C2H5 | 4-CH3-2-CONHCH3 |
2-Cl | 2-OCH3 | 2,4-2CH3 | 4-CH3-2-COCH3 | 4-CF3-2-CONHCH3 |
2-CH3 | 4-CH3 | 4-C(CH3)3 | 4-CH3-2-CO2C2H5 | 2-CH3-4-CO2C2H5 |
2-Br | 2,4-2Cl | 2-CN-4-CF3 | 2-Ph | 2-(4-Cl-Ph) |
表13
R | R | R | R | R |
5-CN | 5-NO2 | 4-CO2C2H5 | 4-CH3-5-COCH3 | 4,5-(CCl=CH-CH=CH-) |
5-Cl | 3,4-2CH3 | 3-COCH3-4-CH3 | 4-CH3-5-CO2C2H5 | 4,5-(CH=CCl-CH=CH-) |
5-CH3 | 5-OCH3 | 4,5-(CH2-)3 | 4-CF3-5-CO2C2H5 | 4,5-(CH=CH-CCl=CH-) |
4-Cl | 4,5-2Cl | 4,5-(CH2-)4 | 5-CH3-4-CO2C2H5 | 4,5-(Cme=CH-CH=CH-) |
3-Cl | 3-CH3 | 3-CO2C2H5 | 3-CF3-5-CO2C2H5 | 4,5-(CH=Cme-CH=CH-) |
5-Br | 4,5-2CH3 | 4-CF3-5-CN | 3-CO2C2H5-4-CF3 | 3,4-(CH=CH-CH=CH-) |
3-Br | 3-OCH3 | 4-CH2CO2C2H5 | 4-CH3-5-CONHCH3 | 4,5-(C(Ome)=CH-CH=CH-) |
3-NO2 | 4-C(CH3)3 | 3-CH2CO2C2H5 | 4-CF3-5-CONHCH3 | 4,5-(CH=C(Ome)-CH=CH-) |
4-CH3 | 3,5-2CH3 | 3,4-(CH2-)4 | 3-CF3-5-CN | 4,5-(CH=CH-CH=CH-) |
表14
R | R | R | R | R |
5-CN | 5-OCH3 | 4-CO2C2H5 | 4-CH3-5-COCH3 | 4,5-(CCl=CH-CH=CH-) |
5-Cl | 4,5-2Cl | 4-CH2CO2C2H5 | 4-CH3-5-CO2C2H5 | 4,5-(CH=CCl-CH=CH-) |
5-CH3 | 2,4-2Cl | 2-CF3-5-CN | 4-CF3-5-CO2C2H5 | 4,5-(CH=CH-CCl=CH-) |
4-Cl | 2,5-2Cl | 4,5-(CH2-)4 | 5-CH3-4-CO2C2H5 | 4,5-(CH=CH-CH=CCl-) |
2-Cl | 2,4-2CH3 | 4-CF3-5-CN | 2-COCH3-4-CH3 | 4,5-(Cme=CH-CH=CH-) |
5-Br | 4-C(CH3)3 | 4,5-(CH2-)3 | 2-CF3-5-CO2C2H5 | 4,5-(CH=Cme-CH=CH-) |
2-Br | 2-OCH3 | 2-CO2C2H5 | 2-CO2C2H5-4-CF3 | 4,5-(C(Ome)=CH-CH=CH-) |
4-CH3 | 4-CF3 | 4,5-2CH3 | 4-CF3-5-CONHCH3 | 4,5-(CH=C(Ome)-CH=CH-) |
5-NO2 | 4-CN | 2,4-2CH3 | 2-CH3-5-COCH3 | 4,5-(CH=CH-CH=CH-) |
2-CH3 | 2-CN | 2,4-2Cl | 4-CH3-5-CONHCH3 | 4,5-(C(NO2)=CH-CH=CH-) |
2-NO2 | 4-NO2 | 2,5-2CH3 | 2-Cl-4-NO2 | 4,5-(CH=C(NO2)-CH=CH-) |
表15
R | R | R |
1-H-5-Cl | 1-CH3-5-Cl | 1-C(CH3)3-5-Br |
1-C(CH3)3-5-Cl | 1-CH3-5-Br | 1-C(CH3)3-5-OCH3 |
1-C2H5-5-Cl | 1-CH(CH3)2-5-Cl | 1-CO2C2H5-5-Cl |
1-(4-Cl-Ph)-5-Cl | 1-(4-Cl-Ph)-5-Br | 1-(4-NO2-Ph)-5-Cl |
本发明中的部分化合物可以用表16中列出的具体化合物来说明,但并不限定本发明。
表16
编号 | Q | n | X | R1 | R2 | R3 |
1 | 5-CF3-2-吡啶基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
2 | 3-Cl-5-CF3-2-吡啶基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
3 | 3-F-5-Cl-2-吡啶基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
4 | 3,5-2Cl-2-吡啶基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
5 | 3-Cl-5-CN-2-吡啶基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
6 | 3-Cl-5-CCl3-2-吡啶基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
7 | 3-Cl-5-CH3-2-吡啶基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
8 | 3-Cl-2-吡啶基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
9 | 2-吡啶基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
10 | 6-Cl-2-吡啶基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
11 | 3,5,6-3Cl-2-吡啶基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
12 | 3-CN-2-吡啶基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
13 | 3-CN-4-CH3-2-吡啶基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
14 | 3-CN-4-CF3-2-吡啶基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
15 | 3-CN-4,6-2CH3-2-吡啶基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
16 | 6-CH3-2-吡啶基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
17 | 5-CH3-2-吡啶基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
18 | 4-CN-2-吡啶基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
19 | 5-Cl-4-CN-3-吡啶基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
20 | 4-CF3-3-CN-6-Cl-2-吡啶基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
21 | 2-Cl-3-CN-4-CF3-6-吡啶基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
22 | 4-CH3-3-CN-6-Cl-2-吡啶基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
23 | 2-Cl-3-CN-4-CH3-6-吡啶基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
24 | 3-CF3-2-吡啶基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
25 | 6-CF3-3-Cl-2-吡啶基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
26 | 2,3-2Cl-4-CF3-6-吡啶基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
27 | 6-CH3-4-嘧啶基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
28 | 6-CF3-4-嘧啶基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
29 | 6-CH3-5-Cl-4-嘧啶基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
30 | 6-C2H5-5-Cl-4-嘧啶基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
31 | 6-CF3-5-Cl-4-嘧啶基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
32 | 6-CH3-5-Cl-2-CH3-4-嘧啶基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
33 | 6-CH3-2-Cl-4-嘧啶基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
34 | 6-CH3-4-Cl-2-嘧啶基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
35 | 6-CH3-2-SCH3-4-嘧啶基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
36 | 3,5-2CH3-2-嘧啶基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
37 | 3,5-OCH3-2-嘧啶基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
38 | 苯基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
39 | 4-CF3-苯基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
40 | 2-Cl-4-CF3-苯基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
41 | 2,6-2Cl-4-CF3-苯基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
42 | 2-NO2-苯基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
43 | 4-NO2-苯基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
44 | 4-NO2-3-CH3-苯基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
45 | 2-NO2-4-CF3-苯基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
46 | 4-CN-2-F-苯基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
47 | 5-Cl-2-苯并恶唑基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
48 | 5-CF3-2-苯并恶唑基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
49 | 5-Cl-2-苯并噻唑基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
50 | 5-CF3-2-苯并噻唑基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
51 | 6-Cl-2-喹喔啉基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
52 | 6-Cl-3-哒嗪基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
53 | 6-CH3-3-哒嗪基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
54 | 5-Cl-2-吡嗪基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
55 | 6-Cl-2-吡嗪基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
56 | 3-CF3-5-吡唑基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
57 | 1-C(CH3)3-5-Cl-4-哒嗪酮基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
58 | 1-CH3-5-Cl-4-哒嗪酮基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
59 | 1-CH3-5-Br-4-哒嗪酮基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
60 | 1-C(CH3)3-5-Br-4-哒嗪酮基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
61 | 4-CF3O-苯基 | 1 | -CH2CH2CH2- | Cl | Cl | H |
62 | 4-CF3-苯基 | 1 | -CH2CH2CH2- | Cl | Cl | H |
63 | 4-C(CH3)3-苯基 | 1 | -CH2CH2CH2- | Cl | Cl | H |
64 | 4-CN-苯基 | 1 | -CH2CH2CH2- | Cl | Cl | H |
65 | 4-Cl-苯基 | 1 | -CH2CH2CH2- | Cl | Cl | H |
66 | 4-F-苯基 | 1 | -CH2CH2CH2- | Cl | Cl | H |
67 | 2-Cl-苯基 | 1 | -CH2CH2CH2- | Cl | Cl | H |
68 | 2-CH3-苯基 | 1 | -CH2CH2CH2- | Cl | Cl | H |
69 | 2,4-2Cl-苯基 | 1 | -CH2CH2CH2- | Cl | Cl | H |
70 | 3,4-2Cl-苯基 | 1 | -CH2CH2CH2- | Cl | Cl | H |
71 | 2,6-2Cl-苯基 | 1 | -CH2CH2CH2- | Cl | Cl | H |
72 | 2-Cl-6-F-苯基 | 1 | -CH2CH2CH2- | Cl | Cl | H |
73 | 4-CH3-苯基 | 1 | -CH2CH2CH2- | Cl | Cl | H |
74 | 4-CH3O-苯基 | 1 | -CH2CH2CH2- | Cl | Cl | H |
75 | 2-CN-苯基 | 1 | -CH2CH2CH2- | Cl | Cl | H |
76 | 2-NO2-苯基 | 1 | -CH2CH2CH2- | Cl | Cl | H |
77 | 苯基 | 1 | -CH2CH2CH2- | Cl | Cl | H |
78 | 2-CF3-5-吡啶基 | 1 | -CH2CH2CH2- | Cl | Cl | H |
79 | 2-Cl-5-吡啶基 | 1 | -CH2CH2CH2- | Cl | Cl | H |
80 | 2-Cl-5-噻唑基 | 1 | -CH2CH2CH2- | Cl | Cl | H |
81 | 5-Cl-3-吲哚基 | 1 | -CH2CH2CH2- | Cl | Cl | H |
82 | 5-F-3-吲哚基 | 1 | -CH2CH2CH2- | Cl | Cl | H |
83 | 5-CF3-2-吡啶基 | 0 | -CH2CH2CH2- | Cl | H | H |
84 | 3-Cl-5-CF3-2-吡啶基 | 0 | -CH2CH2CH2- | Cl | H | H |
85 | 3-F-5-Cl-2-吡啶基 | 0 | -CH2CH2CH2- | Cl | H | H |
86 | 3,5-2Cl-2-吡啶基 | 0 | -CH2CH2CH2- | Cl | H | H |
87 | 3-Cl-2-吡啶基 | 0 | -CH2CH2CH2- | Cl | H | H |
88 | 3,5,6-3Cl-2-吡啶基 | 0 | -CH2CH2CH2- | Cl | H | H |
89 | 3-CF3-2-吡啶基 | 0 | -CH2CH2CH2- | Cl | H | H |
90 | 6-CH3-5-Cl-4-嘧啶基 | 0 | -CH2CH2CH2- | Cl | H | H |
91 | 6-C2H5-5-Cl-4-嘧啶基 | 0 | -CH2CH2CH2- | Cl | H | H |
92 | 6-CF3-5-Cl-4-嘧啶基 | 0 | -CH2CH2CH2- | Cl | H | H |
93 | 苯基 | 0 | -CH2CH2CH2- | Cl | H | H |
94 | 4-CF3-苯基 | 0 | -CH2CH2CH2- | Cl | H | H |
95 | 2-Cl-4-CF3-苯基 | 0 | -CH2CH2CH2- | Cl | H | H |
96 | 2,6-2Cl-4-CF3-苯基 | 0 | -CH2CH2CH2- | Cl | H | H |
97 | 2-NO2-苯基 | 0 | -CH2CH2CH2- | Cl | H | H |
98 | 4-NO2-苯基 | 0 | -CH2CH2CH2- | Cl | H | H |
99 | 4-NO2-3-CH3-苯基 | 0 | -CH2CH2CH2- | Cl | H | H |
100 | 2-NO2-4-CF3-苯基 | 0 | -CH2CH2CH2- | Cl | H | H |
101 | 4-CN-2-F-苯基 | 0 | -CH2CH2CH2- | Cl | H | H |
102 | 5-Cl-2-苯并恶唑基 | 0 | -CH2CH2CH2- | Cl | H | H |
103 | 5-CF3-2-苯并恶唑基 | 0 | -CH2CH2CH2- | Cl | H | H |
104 | 6-Cl-2-喹喔啉基 | 0 | -CH2CH2CH2- | Cl | H | H |
105 | 6-Cl-3-哒嗪基 | 0 | -CH2CH2CH2- | Cl | H | H |
106 | 1-C(CH3)3-5-Cl-4-哒嗪酮基 | 0 | -CH2CH2CH2- | Cl | H | H |
107 | 4-C(CH3)3-苯基 | 1 | -CH2CH2CH2- | Cl | H | H |
108 | 4-CN-苯基 | 1 | -CH2CH2CH2- | Cl | H | H |
109 | 4-Cl-苯基 | 1 | -CH2CH2CH2- | Cl | H | H |
110 | 2,4-2Cl-苯基 | 1 | -CH2CH2CH2- | Cl | H | H |
111 | 2-Cl-6-F-苯基 | 1 | -CH2CH2CH2- | Cl | H | H |
112 | 2-CN-苯基 | 1 | -CH2CH2CH2- | Cl | H | H |
113 | 2-NO2-苯基 | 1 | -CH2CH2CH2- | Cl | H | H |
114 | 苯基 | 1 | -CH2CH2CH2- | Cl | H | H |
115 | 2-Cl-5-吡啶基 | 1 | -CH2CH2CH2- | Cl | H | H |
116 | 2-Cl-5-噻唑基 | 1 | -CH2CH2CH2- | Cl | H | H |
117 | 5-CF3-2-吡啶基 | 0 | -CH2CH2CH2- | Cl | Cl | Cl |
118 | 3-Cl-5-CF3-2-吡啶基 | 0 | -CH2CH2CH2- | Cl | Cl | Cl |
119 | 3-F-5-Cl-2-吡啶基 | 0 | -CH2CH2CH2- | Cl | Cl | Cl |
120 | 3,5-2Cl-2-吡啶基 | 0 | -CH2CH2CH2- | Cl | Cl | Cl |
121 | 3-Cl-2-吡啶基 | 0 | -CH2CH2CH2- | Cl | Cl | Cl |
122 | 3,5,6-3Cl-2-吡啶基 | 0 | -CH2CH2CH2- | Cl | Cl | Cl |
123 | 3-CF3-2-吡啶基 | 0 | -CH2CH2CH2- | Cl | Cl | Cl |
124 | 6-CH3-5-Cl-4-嘧啶基 | 0 | -CH2CH2CH2- | Cl | Cl | Cl |
125 | 6-C2H5-5-Cl-4-嘧啶基 | 0 | -CH2CH2CH2- | Cl | Cl | Cl |
126 | 6-CF3-5-Cl-4-嘧啶基 | 0 | -CH2CH2CH2- | Cl | Cl | Cl |
127 | 苯基 | 0 | -CH2CH2CH2- | Cl | Cl | Cl |
128 | 4-CF3-苯基 | 0 | -CH2CH2CH2- | Cl | Cl | Cl |
129 | 2-Cl-4-CF3-苯基 | 0 | -CH2CH2CH2- | Cl | Cl | Cl |
130 | 2,6-2Cl-4-CF3-苯基 | 0 | -CH2CH2CH2- | Cl | Cl | Cl |
131 | 2-NO2-苯基 | 0 | -CH2CH2CH2- | Cl | Cl | Cl |
132 | 4-NO2-苯基 | 0 | -CH2CH2CH2- | Cl | Cl | Cl |
133 | 4-NO2-3-CH3-苯基 | 0 | -CH2CH2CH2- | Cl | Cl | Cl |
134 | 2-NO2-4-CF3-苯基 | 0 | -CH2CH2CH2- | Cl | Cl | Cl |
135 | 4-CN-2-F-苯基 | 0 | -CH2CH2CH2- | Cl | Cl | Cl |
136 | 5-Cl-2-苯并恶唑基 | 0 | -CH2CH2CH2- | Cl | Cl | Cl |
137 | 5-CF3-2-苯并恶唑基 | 0 | -CH2CH2CH2- | Cl | Cl | Cl |
138 | 6-Cl-2-喹喔啉基 | 0 | -CH2CH2CH2- | Cl | Cl | Cl |
139 | 6-Cl-3-哒嗪基 | 0 | -CH2CH2CH2- | Cl | Cl | Cl |
140 | 1-C(CH3)3-5-Cl-4-哒嗪酮基 | 0 | -CH2CH2CH2- | Cl | Cl | Cl |
141 | 4-C(CH3)3-苯基 | 1 | -CH2CH2CH2- | Cl | Cl | Cl |
142 | 4-CN-苯基 | 1 | -CH2CH2CH2- | Cl | Cl | Cl |
143 | 4-Cl-苯基 | 1 | -CH2CH2CH2- | Cl | Cl | Cl |
144 | 2,4-2Cl-苯基 | 1 | -CH2CH2CH2- | Cl | Cl | Cl |
145 | 2-Cl-6-F-苯基 | 1 | -CH2CH2CH2- | Cl | Cl | Cl |
146 | 2-CN-苯基 | 1 | -CH2CH2CH2- | Cl | Cl | Cl |
147 | 2-NO2-苯基 | 1 | -CH2CH2CH2- | Cl | Cl | Cl |
148 | 苯基 | 1 | -CH2CH2CH2- | Cl | Cl | Cl |
149 | 2-Cl-5-吡啶基 | 1 | -CH2CH2CH2- | Cl | Cl | Cl |
150 | 2-Cl-5-噻唑基 | 1 | -CH2CH2CH2- | Cl | Cl | Cl |
151 | 5-CF3-2-吡啶基 | 0 | -CH2CH2- | Cl | Cl | H |
152 | 3-Cl-5-CF3-2-吡啶基 | 0 | -CH2CH2- | Cl | Cl | H |
153 | 3-F-5-Cl-2-吡啶基 | 0 | -CH2CH2- | Cl | Cl | H |
154 | 3,5-2Cl-2-吡啶基 | 0 | -CH2CH2- | Cl | Cl | H |
155 | 3-Cl-2-吡啶基 | 0 | -CH2CH2- | Cl | Cl | H |
156 | 3,5,6-3Cl-2-吡啶基 | 0 | -CH2CH2- | Cl | Cl | H |
157 | 3-CF3-2-吡啶基 | 0 | -CH2CH2- | Cl | Cl | H |
158 | 6-CH3-5-Cl-4-嘧啶基 | 0 | -CH2CH2- | Cl | Cl | H |
159 | 6-C2H5-5-Cl-4-嘧啶基 | 0 | -CH2CH2- | Cl | Cl | H |
160 | 6-CF3-5-Cl-4-嘧啶基 | 0 | -CH2CH2- | Cl | Cl | H |
161 | 苯基 | 0 | -CH2CH2- | Cl | Cl | H |
162 | 4-CF3-苯基 | 0 | -CH2CH2- | Cl | Cl | H |
163 | 2-Cl-4-CF3-苯基 | 0 | -CH2CH2- | Cl | Cl | H |
164 | 2,6-2Cl-4-CF3-苯基 | 0 | -CH2CH2- | Cl | Cl | H |
165 | 2-NO2-苯基 | 0 | -CH2CH2- | Cl | Cl | H |
166 | 4-NO2-苯基 | 0 | -CH2CH2- | Cl | Cl | H |
167 | 4-NO2-3-CH3-苯基 | 0 | -CH2CH2- | Cl | Cl | H |
168 | 2-NO2-4-CF3-苯基 | 0 | -CH2CH2- | Cl | Cl | H |
169 | 4-CN-2-F-苯基 | 0 | -CH2CH2- | Cl | Cl | H |
170 | 5-Cl-2-苯并恶唑基 | 0 | -CH2CH2- | Cl | Cl | H |
171 | 5-CF3-2-苯并恶唑基 | 0 | -CH2CH2- | Cl | Cl | H |
172 | 6-Cl-2-喹喔啉基 | 0 | -CH2CH2- | Cl | Cl | H |
173 | 6-Cl-3-哒嗪基 | 0 | -CH2CH2- | Cl | Cl | H |
174 | 1-C(CH3)3-5-Cl-4-哒嗪酮基 | 0 | -CH2CH2- | Cl | Cl | H |
175 | 4-C(CH3)3-苯基 | 1 | -CH2CH2- | Cl | Cl | H |
176 | 4-CN-苯基 | 1 | -CH2CH2- | Cl | Cl | H |
177 | 4-Cl-苯基 | 1 | -CH2CH2- | Cl | Cl | H |
178 | 2,4-2Cl-苯基 | 1 | -CH2CH2- | Cl | Cl | H |
179 | 2-Cl-6-F-苯基 | 1 | -CH2CH2- | Cl | Cl | H |
180 | 2-CN-苯基 | 1 | -CH2CH2- | Cl | Cl | H |
181 | 2-NO2-苯基 | 1 | -CH2CH2- | Cl | Cl | H |
182 | 苯基 | 1 | -CH2CH2- | Cl | Cl | H |
183 | 2-Cl-5-吡啶基 | 1 | -CH2CH2- | Cl | Cl | H |
184 | 2-Cl-5-噻唑基 | 1 | -CH2CH2- | Cl | Cl | H |
185 | 5-CF3-2-吡啶基 | 0 | -CH2(CH2)2CH2- | Cl | Cl | H |
186 | 3-Cl-5-CF3-2-吡啶基 | 0 | -CH2(CH2)2CH2- | Cl | Cl | H |
187 | 3-F-5-Cl-2-吡啶基 | 0 | -CH2(CH2)2CH2- | Cl | Cl | H |
188 | 3,5-2Cl-2-吡啶基 | 0 | -CH2(CH2)2CH2- | Cl | Cl | H |
189 | 3-Cl-2-吡啶基 | 0 | -CH2(CH2)2CH2- | Cl | Cl | H |
190 | 3,5,6-3Cl-2-吡啶基 | 0 | -CH2(CH2)2CH2- | Cl | Cl | H |
191 | 3-CF3-2-吡啶基 | 0 | -CH2(CH2)2CH2- | Cl | Cl | H |
192 | 6-CH3-5-Cl-4-嘧啶基 | 0 | -CH2(CH2)2CH2- | Cl | Cl | H |
193 | 6-C2H5-5-Cl-4-嘧啶基 | 0 | -CH2(CH2)2CH2- | Cl | Cl | H |
194 | 6-CF3-5-Cl-4-嘧啶基 | 0 | -CH2(CH2)2CH2- | Cl | Cl | H |
195 | 苯基 | 0 | -CH2(CH2)2CH2- | Cl | Cl | H |
196 | 4-CF3-苯基 | 0 | -CH2(CH2)2CH2- | Cl | Cl | H |
197 | 2-Cl-4-CF3-苯基 | 0 | -CH2(CH2)2CH2- | Cl | Cl | H |
198 | 2,6-2Cl-4-CF3-苯基 | 0 | -CH2(CH2)2CH2- | Cl | Cl | H |
199 | 2-NO2-苯基 | 0 | -CH2(CH2)2CH2- | Cl | Cl | H |
200 | 4-NO2-苯基 | 0 | -CH2(CH2)2CH2- | Cl | Cl | H |
201 | 4-NO2-3-CH3-苯基 | 0 | -CH2(CH2)2CH2- | Cl | Cl | H |
202 | 2-NO2-4-CF3-苯基 | 0 | -CH2(CH2)2CH2- | Cl | Cl | H |
203 | 4-CN-2-F-苯基 | 0 | -CH2(CH2)2CH2- | Cl | Cl | H |
204 | 5-Cl-2-苯并恶唑基 | 0 | -CH2(CH2)2CH2- | Cl | Cl | H |
205 | 5-CF3-2-苯并恶唑基 | 0 | -CH2(CH2)2CH2- | Cl | Cl | H |
206 | 6-Cl-2-喹喔啉基 | 0 | -CH2(CH2)2CH2- | Cl | Cl | H |
207 | 6-Cl-3-哒嗪基 | 0 | -CH2(CH2)2CH2- | Cl | Cl | H |
208 | 1-C(CH3)3-5-Cl-4-哒嗪酮基 | 0 | -CH2(CH2)2CH2- | Cl | Cl | H |
209 | 4-C(CH3)3-苯基 | 1 | -CH2(CH2)2CH2- | Cl | Cl | H |
210 | 4-CN-苯基 | 1 | -CH2(CH2)2CH2- | Cl | Cl | H |
211 | 4-Cl-苯基 | 1 | -CH2(CH2)2CH2- | Cl | Cl | H |
212 | 2,4-2Cl-苯基 | 1 | -CH2(CH2)2CH2- | Cl | Cl | H |
213 | 2-Cl-6-F-苯基 | 1 | -CH2(CH2)2CH2- | Cl | Cl | H |
214 | 2-CN-苯基 | 1 | -CH2(CH2)2CH2- | Cl | Cl | H |
215 | 2-NO2-苯基 | 1 | -CH2(CH2)2CH2- | Cl | Cl | H |
216 | 苯基 | 1 | -CH2(CH2)2CH2- | Cl | Cl | H |
217 | 2-Cl-5-吡啶基 | 1 | -CH2(CH2)2CH2- | Cl | Cl | H |
218 | 2-Cl-5-噻唑基 | 1 | -CH2(CH2)2CH2- | Cl | Cl | H |
219 | 6-Cl-2-苯并恶唑基 | 0 | -CH2CH2CH2- | Cl | Cl | H |
220 | 6-Cl-2-苯并恶唑基 | 0 | -CH2CH2CH2- | Cl | H | H |
221 | 6-Cl-2-苯并恶唑基 | 0 | -CH2CH2CH2- | Cl | Cl | Cl |
222 | 6-Cl-2-苯并恶唑基 | 0 | -CH2CH2- | Cl | Cl | H |
223 | 6-Cl-2-苯并恶唑基 | 0 | -CH2(CH2)2CH2- | Cl | Cl | H |
224 | 6-Cl-2-苯并恶唑基 | 0 | -CH2CH2CH2- | H | H | H |
225 | 5-CF3-2-吡啶基 | 0 | -CH2CH2CH2- | H | H | H |
226 | 3-Cl-5-CF3-2-吡啶基 | 0 | -CH2CH2CH2- | H | H | H |
227 | 3-F-5-Cl-2-吡啶基 | 0 | -CH2CH2CH2- | H | H | H |
228 | 3,5-2Cl-2-吡啶基 | 0 | -CH2CH2CH2- | H | H | H |
229 | 3-Cl-2-吡啶基 | 0 | -CH2CH2CH2- | H | H | H |
230 | 3,5,6-3Cl-2-吡啶基 | 0 | -CH2CH2CH2- | H | H | H |
231 | 3-CF3-2-吡啶基 | 0 | -CH2CH2CH2- | H | H | H |
232 | 6-CH3-5-Cl-4-嘧啶基 | 0 | -CH2CH2CH2- | H | H | H |
233 | 6-C2H5-5-Cl-4-嘧啶基 | 0 | -CH2CH2CH2- | H | H | H |
234 | 6-CF3-5-Cl-4-嘧啶基 | 0 | -CH2CH2CH2- | H | H | H |
235 | 苯基 | 0 | -CH2CH2CH2- | H | H | H |
236 | 4-CF3-苯基 | 0 | -CH2CH2CH2- | H | H | H |
237 | 2-Cl-4-CF3-苯基 | 0 | -CH2CH2CH2- | H | H | H |
238 | 2,6-2Cl-4-CF3-苯基 | 0 | -CH2CH2CH2- | H | H | H |
239 | 2-NO2-苯基 | 0 | -CH2CH2CH2- | H | H | H |
240 | 4-NO2-苯基 | 0 | -CH2CH2CH2- | H | H | H |
241 | 4-NO2-3-CH3-苯基 | 0 | -CH2CH2CH2- | H | H | H |
242 | 2-NO2-4-CF3-苯基 | 0 | -CH2CH2CH2- | H | H | H |
243 | 4-CN-2-F-苯基 | 0 | -CH2CH2CH2- | H | H | H |
244 | 5-Cl-2-苯并恶唑基 | 0 | -CH2CH2CH2- | H | H | H |
245 | 5-CF3-2-苯并恶唑基 | 0 | -CH2CH2CH2- | H | H | H |
246 | 6-Cl-2-喹喔啉基 | 0 | -CH2CH2CH2- | H | H | H |
247 | 6-Cl-3-哒嗪基 | 0 | -CH2CH2CH2- | H | H | H |
248 | 1-C(CH3)3-5-Cl-4-哒嗪酮基 | 0 | -CH2CH2CH2- | H | H | H |
249 | 4-C(CH3)3-苯基 | 1 | -CH2CH2CH2- | H | H | H |
250 | 4-CN-苯基 | 1 | -CH2CH2CH2- | H | H | H |
251 | 4-Cl-苯基 | 1 | -CH2CH2CH2- | H | H | H |
252 | 2,4-2Cl-苯基 | 1 | -CH2CH2CH2- | H | H | H |
253 | 2-Cl-6-F-苯基 | 1 | -CH2CH2CH2- | H | H | H |
254 | 2-CN-苯基 | 1 | -CH2CH2CH2- | H | H | H |
255 | 2-NO2-苯基 | 1 | -CH2CH2CH2- | H | H | H |
256 | 苯基 | 1 | -CH2CH2CH2- | H | H | H |
257 | 2-Cl-5-吡啶基 | 1 | -CH2CH2CH2- | H | H | H |
258 | 2-Cl-5-噻唑基 | 1 | -CH2CH2CH2- | H | H | H |
本发明通式(I)化合物可由如下方法制备,除另有注明外,反应式中各基团定义同前。
通式(I)化合物可以由通式(II)所示的取代的苯酚与通式(III)所示的二卤代丙烯类化合物在碱性条件下缩合制得。
通式(II)所代表的化合物可由通式(IV)所代表的化合物与对苯二酚反应制得。
通式(III)所示的化合物可以由已知方法制得,具体参见CN1860874、US20030073847和WO9727173等。
通式(IV)所示的化合物部分有市售,也可通过已知方法制得,具体参见US4448968、US4528379、EP0344684、US2006148867、JP2004346016、WO2009013195、JP2007091596、CN101056864、US5240940、WO2007088876、US2008280766、WO2009083105、WO2009068652、US2009105308、EP2281812;J.Heterocyclic Chem.,2004,41:381;Arch.Pharm.Chem.Life Sci.2005,338:117-125;J.Med.Chem,1992,35,1299-1318。
通式(III)和(IV)中,L是离去基团,选自氯或溴。
反应在适宜的溶剂中进行,适宜的溶剂可选自如四氢呋喃、乙腈、甲苯、二甲苯、苯、N,N-二甲基甲酰胺、二氯甲烷、三氯甲烷、丙酮或丁酮等。
适宜的碱可选自如氢氧化钾、氢氧化钠、碳酸钠、碳酸钾、碳酸氢钠、三乙胺、吡啶、氢化钠、氢化钾、氨基钠、甲醇钠、乙醇钠、叔丁醇钠或叔丁醇钾等。
反应温度可在室温至溶剂沸点温度之间,通常为20~130℃。
反应时间为30分钟至20小时,通常1~10小时。
本发明的通式(I)化合物对农业、民用和动物技术领域中有害昆虫的成虫、幼虫和卵都显示出高杀虫活性。因此,本发明还包括通式(I)化合物在农业和其他领域中用作制备杀虫剂药物的用途。
尤其是,通式(I)化合物对下列科和目的重要害虫有活性:鳞翅目害虫,如二化螟、稻纵卷叶螟、小菜蛾、甜菜夜蛾、粘虫、斜纹夜蛾等。特别是对小菜蛾、粘虫活性更好,在很低的剂量下就可以获得很好的效果。因此本发明的通式(I)化合物优选在农业和其他领域中用于防治鳞翅目害虫的应用。
由于良好的性能,本发明化合物可有利地用于保护农业和园艺业重要的作物、家畜和种畜,以及人类常去的环境免于有害昆虫的伤害。
为获得理想效果,化合物的用量因各种因素而改变,例如所用化合物、被保护的作物、有害生物的类型、感染程度、气候条件、施药方法、采用的剂型。
每公顷10克-1000克的化合物剂量能提供充分的防治。
本发明的另一目的还涉及通过施用通式(I)化合物,防治农业和园艺业重要的作物和/或家畜和种畜和/或人类常去的环境中的昆虫的方法。化合物的用量在每公顷10克-1000克内变化。
为了实际应用于农业,使用含一种或多种通式(I)化合物的组合物通常是有益的。
因此,本发明的技术方案包括含一种或多种通式(I)化合物作为活性成分的杀虫组合物,组合物中活性成分的重量百分含量为0.1-99%。
组合物的使用形式可以是干粉、可湿性粉剂、乳油、微乳剂、糊剂、颗粒剂、溶液、悬浮剂等:组合物类型的选择取决于具体的应用。
组合物是以已知方法制备的,例如任选在表面活性剂的存在下,通过用溶剂介质和/或固体稀释剂稀释或溶解活性物质。
可用的固体稀释剂或载体是例如:二氧化硅、高岭土、膨润土、滑石、硅藻土、白云石、碳酸钙、氧化镁、白垩、粘土、合成硅酸盐、硅镁土、海泡石等。
除水以外,可用的液体稀释剂还包括如芳族有机溶剂(二甲苯或烷基苯的混合物、氯苯等),石蜡(石油馏分),醇类(甲醇、丙醇、丁醇、辛醇、甘油),酯类(乙酸乙酯、乙酸异丁酯等),酮类(环己酮、丙酮、苯乙酮、异佛尔酮、乙基戊基酮等),酰胺类(N,N-二甲基甲酰胺、N-甲基吡咯烷酮等)。
可用的表面活性剂是烷基磺酸盐、烷基芳基磺酸盐、聚氧乙烯烷基酚、山梨醇的聚氧乙烯酯、木质素磺酸盐等的钠、钙、三乙基胺或三乙醇胺盐。
组合物还可含特殊的添加剂用于特定的目的,例如含有粘合剂如阿拉伯胶、聚乙烯醇、聚乙烯吡咯烷酮等。
上述组合物中活性成分的浓度可根据活性成分、使用目的、环境条件和采用的制剂类型而在宽范围内改变。活性成分的浓度范围通常为0.5-90%,优选5-60%。
如果需要,可以向组合物中添加能与通式(I)化合物兼容的其他活性成分,例如其他杀螨剂/杀虫剂、杀真菌剂、植物生长调节剂、抗生素、除草剂、肥料。
几种常见剂型的配制方法举例如下:
悬浮剂的配制:常用配方中活性组分含量为5-35%。以水为介质,将原药、分散剂、助悬剂和抗冻剂等加入砂磨机中,进行研磨,制成悬浮剂。
水乳剂的配制:将原药、溶剂和乳化剂加在一起,使溶解成均匀油相。将水、抗冻剂等混合一起,成为均一水相。在高速搅拌下,将水相加入到油相或将油相加入到水相,形成分散性良好的水乳剂。本发明的水乳剂活性组分含量一般为5%-15%。为制备浓乳剂,本发明的化合物可溶解于一种或数种混合溶剂,再加入乳化剂来增强化合物在水中的分散效果。
可湿性粉剂的配制:按配方要求,将原药、各种表面活性剂及固体稀释剂等充分混合,经超细粉碎机粉碎后,即得到预定含量(例如10-60%)的可湿性粉剂产品。为制备适于喷洒用的可湿性粉剂,本发明的化合物可以和研细的固体粉末如粘土、无机硅酸盐、碳酸盐以及润湿剂、粘合剂和/或分散剂组成混合物。
水分散性粒剂的配制:将原药和粉状固体稀释剂、润湿展着剂及粘合剂等进行混合粉碎,再加水捏合后,加入装有一定规格筛网的造粒机中进行造粒,然后再经干燥、筛分(按筛网范围)。也可将原药、分散剂、崩解剂和润湿剂及固体稀释剂加入砂磨机中,以水为介质研磨,制成悬浮剂,然后进行喷雾干燥造粒,通常配制含量为20-30%颗粒状产品。
具体实施方式
以下具体实施例用来进一步说明本发明,但本发明绝非仅限于这些例子。(除自制例之外的各例中所用原料均有市售)
合成实施例
实例1:化合物1的制备
(1)4-(5-三氟甲基吡啶-2-基氧基)苯酚的合成
将对苯二酚12.1克(0.11摩尔)、无水碳酸钾15.2克(0.11摩尔)依次加入装有200毫升N,N-二甲基甲酰胺的500毫升三口烧瓶中,升温至60℃形成浅黄色浑浊液,向其中滴加含有18.2克(0.1摩尔)2-氯-5-三氟甲基吡啶的50毫升N,N-二甲基甲酰胺溶液,15分钟滴加完毕,升温至90℃反应4小时,TLC监测反应基本完毕。反应液冷却至室温,倒入300毫升水中,乙酸乙酯(300毫升×2)萃取2次,合并有机相,有机相用饱和食盐水(200毫升×2)洗2次,无水硫酸镁干燥,减压脱溶,残余物柱层析(乙酸乙酯∶石油醚=1∶8)得白色固体19.1克,收率75%。
(2)化合物1的合成
化合物1
将0.77克(3毫摩)4-(5-三氟甲基吡啶-2-基氧基)苯酚、1.23克(3毫摩)2-(3-溴丙氧基)-1,3-二氯-5-(3,3-二氯丙烯氧基)苯(参照WO9604228A1的方法自制)和0.62克(4.5毫摩)无水碳酸钾依次加入装有50毫升乙腈的100毫升单口烧瓶中,升温至回流反应1小时,TLC监测反应完毕。物料冷却至室温,过滤,滤液减压脱溶,残余物柱层析(乙酸乙酯∶石油醚=1∶30)得目标产物1.52克,无色油状物,收率87%。
核磁数据(1HNMR,300MHz,内标TMS,溶剂CDCl3):δppm 8.45(s,1H),7.87(d,1H),7.07(d,2H),6.98(d,2H),6.84(m,1H),6.83(s,2H),6.12(t,1H),4.57(d,2H),4.27(t,2H),4.17(t,2H),2.30(m,2H)。
实例2:化合物2的制备
(1)4-(3-氯-5-三氟甲基吡啶-2-基氧基)苯酚的合成
将对苯二酚12.1克(0.11摩尔)、无水碳酸钾15.2克(0.11摩尔)依次加入装有200毫升丁酮的500毫升三口烧瓶中,升温至回流,形成乳白色浑浊液,向其中滴加含有21.6克(0.1摩尔)2,3-二氯-5-三氟甲基吡啶的50毫升丁酮溶液,15分钟滴加完毕,继续回流反应3小时,TLC监测反应基本完毕。物料冷却至室温,过滤,滤液减压脱溶,残余物柱层析(乙酸乙酯∶石油醚=1∶8)得白色固体24.9克,收率86%。
(2)化合物2的合成
化合物2
将0.87克(3毫摩)4-(3-氯-5-三氟甲基吡啶-2-基氧基)苯酚、1.23克(3毫摩)2-(3-溴丙氧基)-1,3-二氯-5-(3,3-二氯丙烯氧基)苯和0.62克(4.5毫摩)无水碳酸钾依次加入装有50毫升乙腈的100毫升单口烧瓶中,升温至回流反应,2小时后TLC监测反应完毕。物料冷却至室温,过滤,滤液减压脱溶,残余物柱层析(乙酸乙酯∶石油醚=1∶30)得目标产物1.56克,浅黄色油状物,收率84%。
核磁数据(1HNMR,300MHz,内标TMS,溶剂CDCl3):δppm 8.27(s,1H),7.96(s,1H),7.10(d,2H),6.98(d,2H),6.84(s,2H),6.11(t,1H),4.58(d,2H),4.28(t,2H),4.17(t,2H),2.31(m,2H)。
实例3:化合物38的制备
化合物38
将0.56克(3毫摩)4-苯氧基苯酚、1.23克(3毫摩)2-(3-溴丙氧基)-1,3-二氯-5-(3,3-二氯丙烯氧基)苯和0.62克(4.5毫摩)无水碳酸钾依次加入到装有50毫升乙腈的100毫升单口烧瓶中,升温至回流,反应1小时后,TLC监测反应完毕。物料冷却至室温,过滤,滤液减压脱溶,残余物柱层析(乙酸乙酯∶石油醚=1∶20)得目标产物1.22克,浅黄色油状物,收率79%。
核磁数据(1HNMR,300MHz,内标TMS,溶剂CDCl3):δppm 7.30(m,2H),6.89-7.04(m,7H),6.84(s,2H),6.10(t,1H),4.57(d,2H),4.25(t,2H),4.16(t,2H),2.29(m,2H)。
实例4:化合物57的制备
(1)2-叔丁基-4-氯-5-(4-羟基苯氧基)哒嗪-3(2H)-酮的合成
将原料2,3-二氯-5-三氟甲基吡啶替换为2-叔丁基-4,5-二氯哒嗪-3(2H)-酮(22.1克,0.1摩尔),制备方法同实例2中步骤(1),柱层析(乙酸乙酯∶石油醚=1∶5)得浅黄色固体21.2克,收率72%。
(2)化合物57的合成
化合物57
将原料4-(3-氯-5-三氟甲基吡啶-2-基氧基)苯酚替换为2-叔丁基-4-氯-5-(4-羟基苯氧基)哒嗪-3(2H)-酮(0.88克,3毫摩),制备方法同实例1中步骤(2),柱层析(乙酸乙酯∶石油醚=1∶30)得浅黄色油状物1.25克,收率68%。
核磁数据(1HNMR,300MHz,内标TMS,溶剂CDCl3):δppm 7.39(s,1H),7.05(d,2H),6.96(d,2H),6.84(s,2H),6.11(t,1H),4.58(d,2H),4.17(t,2H),4.14(t,2H),2.30(m,2H)。
实例5:化合物72的制备
(1)4-(2-氯-6-氟苄氧基)苯酚的合成
将原料2,3-二氯-5-三氟甲基吡啶替换为2-氯-6-氟苄氯(17.9克,0.1摩尔),制备方法同实例2中步骤(1),柱层析(乙酸乙酯∶石油醚=1∶10)得白色固体21.4克,收率85%。
(2)化合物72的合成
将原料4-(3-氯-5-三氟甲基吡啶-2-基氧基)苯酚替换为4-(2-氯-6-氟苄氧基)苯酚(0.75克,3毫摩),制备方法同实例1中步骤(2),柱层析(乙酸乙酯∶石油醚=1∶30)得无色油状物1.40克,收率81%。
核磁数据(1HNMR,300MHz,内标TMS,溶剂CDCl3):δppm 6.96(m,3H),6.88(m,4H),6.83(s,2H),6.11(t,1H),5.13(s,2H),4.59(d,2H),4.22(t,2H),4.15(t,2H),2.27(m,2H)。
实例6:化合物80的制备
(1)4-((2-氯噻唑-5-基)甲氧基)苯酚的合成
将原料2,3-二氯-5-三氟甲基吡啶替换为2-氯-5-氯甲基噻唑(16.8克,0.1摩尔),制备方法同实例2中步骤(1),柱层析(乙酸乙酯∶石油醚=1∶6)得浅黄色固体17.8克,收率74%。
(2)化合物80的合成
将原料4-(3-氯-5-三氟甲基吡啶-2-基氧基)苯酚替换为4-((2-氯噻唑-5-基)甲氧基)苯酚(0.72克,3毫摩),制备方法同实例1中步骤(2),柱层析(乙酸乙酯∶石油醚=1∶30)得浅黄色油状物1.40克,收率82%。
核磁数据(1HNMR,300MHz,内标TMS,溶剂CDCl3):δppm 7.59(s,1H),6.86(m,4H),6.84(s,2H),6.11(t,1H),5.12(s,2H),4.58(d,2H),4.20(m,4H),2.27(m,2H)。
实例7:化合物219的制备
(1)4-(6-氯苯并恶唑-2-基氧基)苯酚的合成
将原料2,3-二氯-5-三氟甲基吡啶替换为2,6-二氯苯并恶唑(18.8克,0.1摩尔),制备方法同实例2中步骤(1),柱层析(乙酸乙酯∶石油醚=1∶10)得灰色固体22.8克,收率87%。
(2)化合物219的合成
化合物219
将原料4-(3-氯-5-三氟甲基吡啶-2-基氧基)苯酚替换为4-(6-氯苯并恶唑-2-基氧基)苯酚(0.79克,3毫摩),制备方法同实例1中步骤(2),柱层析(乙酸乙酯∶石油醚=1∶30)得浅黄色固体1.32克,收率75%,m.p.80-82℃。
核磁数据(1HNMR,300MHz,内标TMS,溶剂CDCl3):δppm 7.44(m,2H),7.39(m,1H),7.31(d,2H),6.99(d,2H),6.84(s,2H),6.12(t,1H),4.58(d,2H),4.28(t,2H),4.18(t,2H),2.31(m,2H)。
通式(I)的其他化合物可以用本发明提供的制备方法制得。部分化合物的物性和核磁数据见表17。
表17
制剂实施例(各组分加入量均为重量百分含量,活性化合物折百后计量加入)
实例8:30%可湿性粉剂
将化合物1及其他组分充分混合,经超细粉碎机粉碎后,即得到30%的可湿性粉剂产品。
实例9:40%浓悬浮剂
将化合物2及其他组分充分混合,由此得到的浓悬浮剂,用水稀释所得悬浮剂可得到任何所需浓度的稀释液。
实例10:60%水分散性粒剂
将化合物38及其他组分混合粉碎,再加水捏合后,加入10-100目筛网的造粒机中进行造粒,然后再经干燥、筛分(按筛网范围)。
生物活性测定实施例
实例11:杀虫活性测定
用本发明化合物对几种昆虫进行了杀虫活性测定试验。测定方法如下:
待测化合物用丙酮/甲醇(1∶1)的混合溶剂溶解后,用含有0.1%(wt)吐温80的水稀释至所需的浓度。
以小菜蛾、粘虫为靶标,采用airbrush喷雾法进行杀虫活性测定。
(1)、杀小菜蛾的活性测定
测定方法:将甘蓝叶片用打孔器打成直径2cm的叶碟,airbrush喷雾处理的压力为10psi(约合0.7kg/cm2),每叶碟正反面喷雾,喷液量为0.5ml。阴干后每处理接入10头2龄试虫,每处理3次重复。处理后放入25℃、相对湿度60~70%观察室内培养,72小时后调查存活虫数,计算死亡率。
对小菜蛾的部分测试结果如下:
药液浓度为600mg/L时,对小菜蛾2龄幼虫致死率高于80%的化合物有1、2、3、11、38、57、72、80、83、84、117、118、219,其中致死率为100%的化合物有1、2、3、11、38、57、72、80、83、117、219。
药液浓度为50mg/L时,对小菜蛾2龄幼虫致死率高于80%的化合物有1、2、3、11、38、80、83,其中致死率为100%的化合物有1、2、80。
按照以上方法,选取化合物1和化合物2与已知化合物A(WO9604228报道的具有杀虫活性的化合物,下同)及商品化品种pyridalyl进行了杀小菜蛾活性的平行测定。试验结果见表18。
表18杀小菜蛾活性比较
(2)、杀粘虫的活性测定
测定方法:将玉米叶片剪成长2cm的叶段,airbrush喷雾处理的压力为10psi(约合0.7kg/cm2),每叶段正反面喷雾,喷液量为0.5ml。阴干后每处理接入10头2龄试虫,每处理3次重复。处理后放入25℃、相对湿度60~70%观察室内培养,72小时后调查存活虫数,计算死亡率。
对粘虫的部分测试结果如下:
药液浓度为600mg/L时,对粘虫致死率为100%的化合物有3、11、38、57、72、80、83、84、117、118、219。
药液浓度为100mg/L时,对粘虫致死率高于90%的化合物有3、11、38、57、72、80、83、84、117、118、219。其中致死率为100%的化合物38、84、117、118、219。
按照以上方法,选取化合物117和化合物219与已知化合物A进行了杀粘虫活性的平行测定。试验结果见表19。
表19杀粘虫活性比较
Claims (9)
1.一种芳氧基二卤丙烯醚类化合物,如通式(I)所示:
式中:
R1、R2、R3可相同或不同,分别选自H、卤素、C1-C8烷基或C3-C8环烷基;
X选自-CH2-、-CH2CH2-、-CH2CH2CH2-、-CH2CH2CH2CH2-、-CH2CH2CH2CH2CH2-、-CH(CH3)-、-CH(CH3)CH2-、-CH(CH3)CH2CH2-、-CH2CH2CH(CH3)-、-CH(C2H5)-、-C(CH3)2-、-CH(CH3)CH(CH3)-、-CH2C(CH3)2CH2-、-CH2CH2OCH2CH2-、-CH2CH2NHCH2CH2-、-CH2CH2SCH2CH2-、-CH2CH2SO2CH2CH2-、-CH2CH(OH)CH2-或-CH2COCH2-;
Q选自芳基或杂芳基,或者所述的芳基或杂芳基环上含有1-4个相同或不同的下述取代基:卤素、CN、NO2、羟基、C1-C8烷基、C3-C8环烷基、C1-C8卤代烷基、C1-C8烷氧基、C1-C8卤代烷氧基、C2-C8烯基、C2-C8炔基、C2-C8卤代烯基、C2-C8卤代炔基、C2-C8烯氧基、C2-C8炔氧基、C2-C8卤代烯氧基、C2-C8卤代炔氧基、芳基、COR5、CO2R4、CONR4R5、NR4R5、NR4COR5、NR5COR4、NR5CO2R4、NR5SO2R4、SOR5、SO2R5、SR5或SO2NR4R5;
R4选自H、C1-C8烷基、C1-C8卤代烷基或C3-C8环烷基;
R5选自H、C1-C8烷基、C1-C8卤代烷基,C3-C8环烷基、未取代或取代的芳基、未取代或取代的杂芳基,所述的取代基选自1-4个相同或不同的下述基团:卤素、CN、NO2、C1-C8烷基、C1-C8卤代烷基、C1-C8烷氧基、C1-C8卤代烷氧基、C1-C8烷氧基羰基或C1-C8烷基磺酰基;
n选自0、1或2。
2.按照权利要求1所述的化合物,其特征在于:通式(I)中
R1、R2、R3可相同或不同,分别选自H或卤素;
X选自-CH2-、-CH2CH2-、-CH2CH2CH2-、-CH2CH2CH2CH2-、-CH2CH2CH2CH2CH2-、-CH2CH(OH)CH2-或-CH2COCH2-;
Q选自芳基或杂芳基,或者所述的芳基或杂芳基环上含有1-4个相同或不同的下述取代基:卤素、CN、NO2、羟基、C1-C8烷基、C3-C8环烷基、C1-C8卤代烷基、C1-C8烷氧基、C1-C8卤代烷氧基、C2-C8烯基、C2-C8炔基、C2-C8卤代烯基、C2-C8卤代炔基、C2-C8烯氧基、C2-C8炔氧基、C2-C8卤代烯氧基、C2-C8卤代炔氧基、CO2R4、NR5SO2R4、SO2R5或SR5;
R4选自H、C1-C4烷基、C1-C4卤代烷基或C3-C6环烷基;
R5选自H、C1-C4烷基、C1-C4卤代烷基或C3-C6环烷基;
n选自0、1或2。
3.按照权利要求2所述的化合物,其特征在于:通式(I)中
R1、R2、R3可相同或不同,分别选自H、Cl或Br;
X选自-CH2-、-CH2CH2-、-CH2CH2CH2-、-CH2CH2CH2CH2-或-CH2CH2CH2CH2CH2-;
Q选自吡咯基、呋喃基、噻吩基、咪唑基、吡唑基、恶唑基、噻唑基、异恶唑基、异噻唑基、苯基、吡啶基、嘧啶基、哒嗪基、吡嗪基、哒嗪酮基、吲哚基、苯并呋喃基、苯并恶唑基、苯并噻吩基、苯并噻唑基、苯并异恶唑基、苯并异噻唑基、苯并咪唑基、苯并吡唑基或喹喔啉基,或者被1-3个独立选自以下基团进一步取代的上述基团:卤素、CN、NO2、羟基、C1-C8烷基、C3-C8环烷基、C1-C8卤代烷基、C1-C8烷氧基、C1-C8卤代烷氧基、C1-C4烷基硫基、C2-C6烯基、C2-C6炔基、C2-C6卤代烯基、C2-C6卤代炔基、C2-C6烯氧基、C2-C6炔氧基、C2-C6卤代烯氧基或C2-C6卤代炔氧基;
n选自0或1。
4.按照权利要求3所述的化合物,其特征在于:通式(I)中
R1、R2、R3可相同或不同,分别选自H或Cl;
X选自-CH2-、-CH2CH2-、-CH2CH2CH2-或-CH2CH2CH2CH2-;
Q选自咪唑基、吡唑基、恶唑基、噻唑基、异恶唑基、异噻唑基、苯基、吡啶基、嘧啶基、哒嗪基、哒嗪酮基、吲哚基、苯并呋喃基、苯并恶唑基、苯并噻唑基、苯并异恶唑基、苯并异噻唑基、苯并咪唑基、苯并吡唑基或喹喔啉基,或者被1-3个独立选自以下基团进一步取代的上述基团:卤素、CN、NO2、羟基、C1-C4烷基、C3-C6环烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷基硫基、C2-C4烯基、C2-C4炔基、C2-C4卤代烯基、C2-C4卤代炔基、C2-C4烯氧基、C2-C4炔氧基、C2-C4卤代烯氧基或C2-C4卤代炔氧基;
n选自0或1。
5.按照权利要求4所述的化合物,其特征在于:通式(I)中
R1、R2、R3可相同或不同,分别选自H或Cl;
X选自-CH2-、-CH2CH2-、-CH2CH2CH2-或-CH2CH2CH2CH2-;
Q选自噻唑基、苯基、吡啶基、嘧啶基、哒嗪基、哒嗪酮基、苯并恶唑基、苯并异噻唑基或喹喔啉基,或者被1-3个独立选自以下基团进一步取代的上述基团:F、Cl、Br、I、CN、NO2、羟基、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷基硫基、C2-C4烯基、C2-C4炔基、C2-C4卤代烯基、C2-C4卤代炔基、C2-C4烯氧基或C2-C4炔氧基;
n选自0或1。
6.按照权利要求5所述的化合物,其特征在于:通式(I)中
R1、R2、R3可相同或不同,分别选自H或Cl;
X选自-CH2CH2CH2-;
Q选自噻唑基、苯基、吡啶基、嘧啶基、哒嗪基、哒嗪酮基、苯并恶唑基、苯并异噻唑基或喹喔啉基,或者被1-3个独立选自以下基团进一步取代的上述基团:F、Cl、Br、CN、NO2、CH3、C2H5、C(CH3)3、CF3、CHFCH3、CHF2、OCH3、OCF3、OCHF2或SCH3;
n选自0或1。
7.按照权利要求6所述的化合物,其特征在于:通式(I)中
R1、R2、R3可相同或不同,分别选自H或Cl;
X选自-CH2CH2CH2-;
Q选自噻唑基、苯基、吡啶基、哒嗪酮基或苯并恶唑基,或者被1-3个独立选自以下基团进一步取代的上述基团:F、Cl、Br、CH3、C2H5、C(CH3)3、CF3、CHFCH3或CHF2;
n选自0或1。
8.一种按照权利要求1所述的通式(I)化合物在农业或其他领域中用作制备杀虫剂药物的用途。
9.一种杀虫组合物,其特征在于:含有如权利要求1所述的通式(I)化合物作为活性组分,组合物中活性组分重量百分含量为0.1-99%。
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CN104738079A (zh) * | 2013-12-26 | 2015-07-01 | 中国中化股份有限公司 | 一种二元杀虫剂组合物及其用途 |
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CN105566148B (zh) * | 2014-10-14 | 2017-10-03 | 沈阳中化农药化工研发有限公司 | 一种季铵盐类化合物及其应用 |
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CN104744352B (zh) * | 2013-12-25 | 2017-08-04 | 沈阳中化农药化工研发有限公司 | 一种制备4‑取代氧基苯酚类化合物的方法 |
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CN105724395A (zh) * | 2014-12-09 | 2016-07-06 | 沈阳中化农药化工研发有限公司 | 一种二元杀虫剂组合物及其应用 |
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CN105766916A (zh) * | 2014-12-23 | 2016-07-20 | 沈阳中化农药化工研发有限公司 | 一种杀虫制剂及其应用 |
CN105766916B (zh) * | 2014-12-23 | 2018-12-14 | 沈阳中化农药化工研发有限公司 | 一种杀虫制剂及其应用 |
CN107298652A (zh) * | 2016-04-14 | 2017-10-27 | 湖南化工研究院有限公司 | 二卤丙烯醚类化合物及其制备与应用 |
CN107298652B (zh) * | 2016-04-14 | 2020-05-19 | 湖南化工研究院有限公司 | 二卤丙烯醚类化合物及其制备与应用 |
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US8969332B2 (en) | 2015-03-03 |
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